Soluble fatty acid condensation products



'15 further heatmg A simflar result is secured by 160 g. of ricinoleic acid are mixed and warmed up to some extent, benzaldehyde. Phenol is the most Patented Aug 22, 1933 g A 1 924 052 SOLUBLE FATTY ACID CONDENSATION PRODUCTS Ian G. Somervllle, Fox Chase, Pa., assignor to Bohm & Haas Company, a Corporation of Delaware No Drawing. Application May 9, 1930 Serial No. 451,199

15 Claims. (Cl. 260-4) This invention relates to sulphonated condenand textile industries. They act as dispersing sation products of fatty acids with phenol-aldeagents for dyestuffs. hydic condensed compounds, which new com- The invention is illustrated by the following pounds have valuable taming properties. One examples but is in no way confined to these ex- 5 such product has been fully described in co-pendamples. 55

ing application #367,633 filed May 31, 1929, of Example 1 which this application is a continuation in part.

The combination of phenols with aldehydes has (a) phenol; 225 formaldehyd? long been known in the process of resin making. are Imxed m 2 /2 of 50% sulphunc mm The type of product obtained is dependent on the g g t g on wfter ig conditions employed. With a low proportion of f .5 1? gf I; g um n s aldehyde to phenol, in presence of an alkaline cat- 1 0 f re fi occurs alyst, a less reactive product is obtained, which gg gfii 33: 3 3 f; iggg fiz gi ii g has not so much tendency to polymerization on (b) g. of clear 1i qui d obtained as above,

use of an acid rather than an alkaline catalyst.

together with mechanical stirring to 100 C. in By using less than 1.0 molecule of aldehyde to 1.0 12 inutes and then to C. in 43 utes.

molecule of phenol I can obtain an intermediate condensation product whose further reaction can gfi gg obtamed 15 clear when Sohdlfied after j g g g g ifggggh gg f ggg fi g a hqmd (c) T0490 g. of resin obtained as above,' 490 cc. 70

While formaldehyde is the most reactive, any of oieum is Slowly F i whfle 001mg the of the lower members of the aliphatic series of zfiz z ita g g g i g fig 1 i i aldehydes may be used in this process, and also 1 S y g w 6 am i the low temperature for 8 hours slow sulphonation occurs. The temperature of. the bath outside is convenient starting material, though homologues then raised to 60 C. for 8 hours, when sulphona $rsifihfiefi$iifi product can now be z complete?!" condensed by heating to a high temperature with g g gs gg ggg gagmgis rggg preferably a long chain, unsaturated fatty acid, 364 caustic gods g when a resinous material is formed. Condensag solution obtained can be used directl tion will take place with unsaturated fatty acids in tanning y of short chain suchas crotonic acid, but in general superior products are obtained when long Example 2 '35 chainunsaturatedacidssuchasoleic are employed. To a mixture of 470 g. of phenol, 2.5 cc. of

Provided that the proportions of material used Sulphuric acid heated to iS w y dd d and conditions chosen have been suitably adjust- With t rring, 235 g. o formaldehyde utio ed, the resin obtained can be sulphonated to give The mixture is Stirred and heated at C- a water soluble product by means of concentrated for one hour- The S'tarting materials are 40 sulphuric acid, oleum, chlorosulphonic acid or removed by steam distillation and decantation. 90

The product is a soft viscous resin. This is conother strong sulphonatmg agent, such as sulphuric acid in presence of glacial acetic acid. densed with oleic acid by mixing the resin with 198 of oleic acid and heatin at 250 C. for 5 In thls W a new class of compounds 15 houfs with stirring. The temgerature is finally i w t compounds P valuable tannmg raised momentarily to 300 C. When cold the Propertles m aqueous sollltlon- They may also be product is a clear, transparent, hard, brittle resin. used as mordants for basic dyes, and, alternative- It is sulphonated in t following manner; 1y ass t the penetration of ac d or di ct es The resin is dissolved in twice its weight of on leather. They find application as wetting, glacial acetic acid. The temperature of the solu- 50 cleansing, and emulsifying agents, in the leather tion is kept below 20 C. while 750 g. of concentrated sulphuric acid is slowly added with stirring. The temperature is raised to 100 C. and held at this point for 3 hours. The mixture is diluted with an equal volume of water and steam distilled to remove the acetic acid. The excess sulphuric acid is removed with calcium hydroxide. I

The solution obtained can be used directly in tanning.

Example 3 Example 4' The soft resin prepared as in Example 2 is condensed with crotonic acid by mixing it with 60 g. of crotonic acid and heating at 150 C. for 5 hours. The temperature is finally raised momentarily to 300 C. When cold the product is a clear, transparent, hard, brittle resin. It is sulphonated by the method of Example 2 or 3.

Example 5 A mixture of 470 g. of phenol 132 g. of acetaldehyde 120 cc. of water 37 cc. of concentrated sulphuric acid is heated cautiously during the first stages of the reaction and is then refluxed for 5 hours. The unused materials are removed by steam distillation and decantation. The soft resin is condensed with oleic acid by mixing the resin with 1'70 g. of oleic acid and heatingat 250 C. for 5 hours. The product is dissolved in twice its weight of glacial acetic acid and sulphonated as in Example 2.

It is understood that deviations in the above examples are possible without departing from the spirit of this invention. Anyone versed in the art will recognize that temperatures, pressures, proportions of ingredients, sequence of operation, etc., can be varied. Condensing with an unsaturated fatty acid, the condensation product of a phenol and an aldehyde, temperatures over 200 C. are preferable though not absolutely necessary. The temperature at which the phenol aldehyde condensation takes place can also be varied within rather wide limitations, the preferred temperature range being between 70 to 110 C. It is understood that the invention is in no way to be confined except as limited by the following claims.

I claim 1. As new compositions of matter, the water soluble products formed by condensing a phenol with an aldehyde, then condensing this product with an unsaturated fatty acid to form a resinous material, finally sulphonating this resin.

2. As new compositions of matter, the water soluble products formed by condensing a phenol with an aldehyde, then condensing this product at over 200 C. with an unsaturated fatty acid to form a resinous material, finally sulphonating this resin.

3. As new compositions of matter, the water soluble products formed by condensing a phenol with an aldehyde in presence of a relatively small amount of mineral acid, then condensing this product at over 200 C. with an unsaturated fatty acid containing more than ten carbon atoms to form a resinous material, finally sulphonating this resin.

4. As new compositions of matter, the water soluble products formed by condensing a phenol with an aldehyde in presence of a relatively small 'amount'of mineral acid, then condensing this product at over 200 C. with oleic acid to form a resinous material, finally sulphonating this resin.

5 As new compositions of matter, the water soluble products formed by condensing phenol with an aldehyde in presence of a relatively small amount of mineral acid, then condensing this product at over 200 C. with an unsaturated fatty acid containing more than ten carbon atoms to form a resinous material, finally sulphonating this resin.

6. As new compositions of matter, the water soluble products formed by condensing phenol with an aldehyde in presence of a relatively small amount of mineral acid, then condensing this product at over 200 C. with oleic acid to form a resinous material, finally sulphonating this resin.

7. As new compositions of matter, the water soluble products formed by condensing phenol with formaldehyde in presence of a relatively small amount of mineral acid, then condensing this product at over 200 C. with an unsaturated,

fatty acid containing more than ten carbon atoms to form a resinous material, finally sulphonating this resin.

8. As a new product the compound formed by condensing phenol with formaldehyde in presence of a relatively small amount of mineral acid, then condensing this product at over 200 C. with oleic acid to form a resinous material, finally sulphonating this resin to give a water soluble prodnet.

9. As a new product the compound formed by condensing phenol with formaldehyde in presence of a small amount of mineral acid at temperatures in the range 70 to 110 C., then condensing this product at temperatures over 200 C. with oleic acid to form a resinous material, finally sulphonating this resin to give a water soluble product.

10. As new compositions of matter, the water soluble products formed by condensing a phenol with an aldehyde then condensing this product at temperatures of substantially200 C. to 300 C. with an unsaturated fatty acid to form a resinous material and finally sulphonating this product.

11. As new compositions of matter, the water soluble products formed by condensing a phenol with an aldehyde in the presence of a relatively small amount of mineral acid then condensing this product at temperatures of substantially 200 C. to 300 C. with an unsaturated fatty acid to form a resinous material and finally sulphonating the product.

12. As new compositions of matter, the water soluble products formed by condensing a phenol with an aldehyde then condensing this product at over 200 C. with an unsaturated fatty acid containing 18 carbon atoms to form a resinous material and finally sulphonating this resin.

13. As new compositions of matter, the water soluble products formed by condensing a phenol with an aldehyde in the presence of a relatively small amount of mineral acid then condensing this product at over 200 C. with an unsaturated fatty acid containing 18 carbon atoms to form soluble product formed by condensing phenol with formaldehyde in the presence of a small amount of acid then condensing this product at over 200 C. with ricinoleic acid to form a resinous material and finally sulphonating this resin.

IAN C. SOMERVIIJE 

